EP0669315B1 - Ortho-substituierte Phenylessigsäureamide - Google Patents

Ortho-substituierte Phenylessigsäureamide Download PDF

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Publication number
EP0669315B1
EP0669315B1 EP95106286A EP95106286A EP0669315B1 EP 0669315 B1 EP0669315 B1 EP 0669315B1 EP 95106286 A EP95106286 A EP 95106286A EP 95106286 A EP95106286 A EP 95106286A EP 0669315 B1 EP0669315 B1 EP 0669315B1
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Prior art keywords
alkyl
phenyl
alkenyl
group
alkoxy
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EP95106286A
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German (de)
English (en)
French (fr)
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EP0669315A1 (de
Inventor
Siegbert Dr. Brand
Eberhard Dr. Ammermann
Gisela Dr. Lorenz
Hubert Dr. Sauter
Klaus Dr. Oberdorf
Uwe Dr. Kardorff
Christoph Dr. Künast
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BASF SE
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BASF SE
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    • C07—ORGANIC CHEMISTRY
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/53—Nitrogen atoms
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    • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
    • C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
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    • C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
    • C07C235/76—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
    • C07C235/78—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
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    • C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/76—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
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    • C07C323/46—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
    • C07C323/47—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to oxygen atoms
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    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
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    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • the invention also relates to processes for the preparation of these compounds I.1-I.7, their use as fungicides and fungicidal agents and pesticides which comprise these compounds as active substances.
  • the invention was based on new fungicidally active ortho-substituted phenylacetic acid derivatives and new insecticidal, acaricidal and nematicidal active substances.
  • ortho-substituted phenylacetic acid amides I can be found in Table 1, compounds with R 2 , R 3 hydrogen, R 4 methyl, R 5 hydrogen and R methyl being particularly preferred.
  • 2-Methoxyimino-2- [2 '- (o - methylphenoxymethyl) phenyl] acetic acid-N-methylamide and 2-methoxyimino-2- (2' - (o-methylphenoxymethyl) phenylacetic acid N-methoxyamide) are very particularly suitable .
  • the ortho-substituted phenylacetic acid amides I can be obtained in various ways, preferably by one of the following methods:
  • L means halogen, especially chlorine and bromine, or C 1 -C 4 alkoxy, especially methoxy.
  • reaction is normally carried out according to methods known per se (e.g. Organikum, 16th edition 1985, pages 409 to 412) in an inert solvent or diluent, advantageously in the presence of a base.
  • Particularly suitable solvents or diluents are chlorinated hydrocarbons such as dichloromethane, ethers such as dioxane and alcohols such as methanol and ethanol.
  • Suitable bases are, for example, alkali metal hydroxides such as sodium and potassium hydroxide, alkali metal carbonates such as sodium and potassium carbonate, alkali metal alcoholates such as sodium methylate and sodium ethylate, in particular tertiary amines such as triethylamine and heteroaromatic amines such as pyridine and 4-dimethylaminopyridine.
  • alkali metal hydroxides such as sodium and potassium hydroxide
  • alkali metal carbonates such as sodium and potassium carbonate
  • alkali metal alcoholates such as sodium methylate and sodium ethylate
  • tertiary amines such as triethylamine and heteroaromatic amines
  • pyridine and 4-dimethylaminopyridine 4-dimethylaminopyridine.
  • reaction temperature is between 0 and 120 ° C, especially at the boiling point of the solvent.
  • the reaction can also be carried out in a 2-phase system with phase transfer catalysis.
  • a mixture of a chlorinated hydrocarbon such as methylene chloride, aqueous alkali, e.g. Sodium hydroxide solution, and a phase transfer catalyst such as tetra-n-butylammonium hydroxide can be used. In this case one works e.g. at temperatures between 10 ° C and the boiling point of one of the components of the solvent mixture.
  • Phenylacetic acid derivatives II, where L is halogen are known or can be prepared by known processes (e.g. Organikum, 16th edition 1985, pages 415, 622 and 423).
  • LC denotes 1 -C 4 alkoxy are known from patent applications EP-A 253 213 and EP-A 254 426 or can be prepared by analogous processes.
  • the hydrolysis of the phenylacetonitriles IV is usually carried out by acid or base catalysis by methods known per se (cf., for example, Beckwith in: Zabicky "The chemistry of Amides” pages 119 to 125 (1970) and Synthesis, 243 (1980)] in an inert solution or diluent.
  • Alcohols such as tert-butanol and ethylene glycol are particularly suitable as solvents.
  • Concentrated mineral acids such as hydrochloric acid, sulfuric acid and phosphoric acid are preferred as acids, and alkali metal hydroxides such as sodium and potassium hydroxide are preferred as bases.
  • the reaction temperature is normally between 0 and 200 ° C., in particular between 20 ° C. and the boiling point of the solvent.
  • the ortho-substituted phenylacetic acid amides I, where R 4 and R 5 are hydrogen, can be alkylated on nitrogen of the amide group by processes known per se [eg Challis in: Zabicky "The Chemistry of Amides", pages 731 to 857 (1970)]:
  • Alk means C 1 -C 4 alkyl
  • X means halogen, especially bromine and iodine.
  • the phenylacetic acid amides I, where R 4 and R 5 are hydrogen are converted into the anions in an inert solvent or diluent by means of a base, and these are reacted with an alkyl halide, preferably an alkyl iodide.
  • Preferred solvents or diluents are ethers such as tetrahydrofuran and dioxane.
  • Alkali metal hydroxides such as sodium and potassium hydroxide and alkali metal hydrides such as sodium and potassium hydride are particularly suitable as bases.
  • reaction temperature is between 0 and 100 ° C, especially at the boiling point of the solvent.
  • the ortho-substituted phenylacetic acid amides I are suitable as fungicides and for controlling pests such as insects, nematodes and acaridia.
  • the ortho-substituted phenylacetic acid amides I are notable for excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes and Basidiomycetes. Some of them are systemically effective and can be used as foliar and soil fungicides.
  • the compounds are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally active amount of the active compounds. It is used before or after the infection of the materials, plants or seeds by the fungi.
  • the ortho-substituted pgenylacetic acid amides I are furthermore suitable for controlling pests from the class of the insects, arachnids and nematodes. They can be used as pesticides in crop protection as well as in the hygiene, protection of stocks and veterinary sectors.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the application forms depend on the purposes; in any case, they should ensure a fine and uniform distribution of the ortho-substituted phenylacetic acid amide.
  • the formulations are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, and in the case of water as diluent other organic solvents can also be used as auxiliary solvents.
  • Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water.
  • emulsions, pastes or oil dispersions the substances as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • concentrates composed of an active substance, wetting agents, adhesives, dispersants or emulsifiers and possibly solvents or oil, which are suitable for dilution with water.
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • the active substance concentrations in the ready-to-use preparations can be varied over a wide range.
  • the agents contain between 0.0001 and 95, preferably between 0.01 and 90% by weight of active ingredient.
  • Formulations with more than 95% by weight of active ingredient can be applied successfully with the ultra-low-volume process (ULV), and even the active ingredient can be used without additives.
  • UUV ultra-low-volume process
  • Granules e.g. Coating, impregnation and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are e.g. Mineral soils, such as silica gel, silicas, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as corn flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
  • Mineral soils such as silica gel, silicas, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomi
  • the application rates in fungicidal compositions are between 0.02 and 3 kg of active ingredient per ha.
  • the new compounds can also be used in material protection (wood protection), e.g. against Paecilomyces variotii.
  • active ingredient 0.001 to 50 g, preferably 0.01 to 10 g, per kg of seed are generally required.
  • the application rate of active ingredient for controlling insects is 0.02 to 10, preferably 0.1 to 2.0 kg / ha under field conditions.
  • compositions according to the invention can also be present together with other active ingredients, for example with herbicides, insecticides, growth regulators, fungicides or else with fertilizers.
  • active ingredients for example with herbicides, insecticides, growth regulators, fungicides or else with fertilizers.
  • These agents can be added to the agents according to the invention in a weight ratio of 1:10 to 10: 1, if appropriate also only immediately before use (tank mix). When mixed with fungicides or insecticides, the spectrum of action is increased in many cases.
  • agents or the ready-to-use preparations produced therefrom such as solutions, emulsions, suspensions, powders, dusts, pastes or granules, are used in a known manner, for example by spraying, atomizing, dusting, scattering, pickling or pouring.
  • Table 1 also lists further end products I which were produced or can be produced in the same ways.
  • Leaves of pot vines of the "Müller-Thurgau" variety were treated with 0.025% by weight aqueous suspensions containing 80% by weight of active ingredient (the active ingredients according to Table Examples 83, 85, 89, 91, 225, 235, 411, 450, 451 and 522) and 20 wt .-% emulsifier contained in the dry substance, sprayed.
  • active ingredient the active ingredients according to Table Examples 83, 85, 89, 91, 225, 235, 411, 450, 451 and 522
  • 20 wt .-% emulsifier contained in the dry substance sprayed.
  • the plants were placed in a greenhouse for 8 days after the spray coating had dried on. Only then were the leaves infected with a spore suspension of Plasmopara viticola (vine peronospora) and the plants placed in a water-saturated chamber at 24 ° C for 48 hours.
  • the vines were then cultivated for 5 days in a greenhouse at temperatures between 20 and 30.degree. C. and again in the moist chamber for 16 hours in order to accelerate the sporangium carrier outbreak. The extent of the fungal attack on the undersides of the leaves was then assessed.
  • Leaves of potted wheat seedlings of the "Schart” variety were containing 0.025% by weight aqueous active ingredient preparations, 80% by weight active ingredient (the active ingredients according to Table Examples 411 and 523) and 20% by weight emulsifier in the dry matter, sprayed and dusted with spores of wheat mildew (Erysiphe graminis var. tritici) 24 hours after the spray coating had dried on.
  • the test plants were then placed in a greenhouse at temperatures between 20 and 22 ° C and 75 to 80% relative humidity. After 7 days the extent of mildew development was assessed.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Pest Control & Pesticides (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Furan Compounds (AREA)
  • Cephalosporin Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Fats And Perfumes (AREA)
EP95106286A 1990-09-22 1991-09-07 Ortho-substituierte Phenylessigsäureamide Expired - Lifetime EP0669315B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4030038A DE4030038A1 (de) 1990-09-22 1990-09-22 Ortho-substituierte phenylessigsaeureamide
DE4030038 1990-09-22
EP91115145A EP0477631B1 (de) 1990-09-22 1991-09-07 Ortho-substituierte Phenylessigsäureamide

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
EP91115145.4 Division 1991-09-07

Publications (2)

Publication Number Publication Date
EP0669315A1 EP0669315A1 (de) 1995-08-30
EP0669315B1 true EP0669315B1 (de) 1997-08-06

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EP91115145A Expired - Lifetime EP0477631B1 (de) 1990-09-22 1991-09-07 Ortho-substituierte Phenylessigsäureamide
EP95106286A Expired - Lifetime EP0669315B1 (de) 1990-09-22 1991-09-07 Ortho-substituierte Phenylessigsäureamide

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KR (1) KR100188986B1 (ja)
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DE (3) DE4030038A1 (ja)
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GR (1) GR3024520T3 (ja)
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EP3378313A1 (en) 2011-03-23 2018-09-26 Basf Se Compositions containing polymeric, ionic compounds comprising imidazolium groups
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BR122019015134B1 (pt) 2012-06-20 2020-04-07 Basf Se mistura pesticida, composição, composição agrícola, métodos para o combate ou controle das pragas de invertebrados, para a proteção dos vegetais em crescimento ou dos materias de propagação vegetal, para a proteção de material de propagação vegetal, uso de uma mistura pesticida e métodos para o combate dos fungos fitopatogênicos nocivos e para proteger vegetais de fungos fitopatogênicos nocivos
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JP3388765B2 (ja) 2003-03-24
DE59106935D1 (de) 1996-01-04
US5677347A (en) 1997-10-14
AU8465691A (en) 1992-03-26
HU211029B (en) 1995-09-28
EP0477631B1 (de) 1995-11-22
IL99113A (en) 1995-11-27
CZ293591B6 (cs) 2004-06-16
HUT58691A (en) 1992-03-30
AU637527B2 (en) 1993-05-27
EP0477631A1 (de) 1992-04-01
DE59108820D1 (de) 1997-09-11
ATE156478T1 (de) 1997-08-15
JPH04288045A (ja) 1992-10-13
CA2049162C (en) 2004-01-13
KR100188986B1 (ko) 1999-06-01
SK280714B6 (sk) 2000-06-12
EP0669315A1 (de) 1995-08-30
CA2049162A1 (en) 1992-03-23
GR3024520T3 (en) 1997-11-28
KR920006300A (ko) 1992-04-27
CS287291A3 (en) 1992-04-15
US5516804A (en) 1996-05-14
ZA917510B (en) 1993-03-22
ATE130598T1 (de) 1995-12-15
DK0669315T3 (da) 1997-09-15
ES2106593T3 (es) 1997-11-01
HU913023D0 (en) 1992-01-28
IL99113A0 (en) 1992-07-15
DE4030038A1 (de) 1992-03-26
US5395854A (en) 1995-03-07
NZ239853A (en) 1993-11-25
US5523454A (en) 1996-06-04

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